Bob was taught by and getting advice from one of the best teachers of entrepreneurship, if such a thing can be taught, and he was still falling short.
Not only was Bob unable to get away from himself, he wasn't able to take advice from a seasoned entrepreneur and do a 'leap of faith'. I'm sorry, but if Steve Blank gave me valuable advice and I was starting my first company you had better bet I'd do more than stare blankly at him.
Bob will never start his own company.
Some people just have to learn some things the hard way. You can coach, advise, mentor all you want and they will just stubbornly do what they are going to do until they figure out for themselves that it's not working.
My 15 year old is like that. It's quite frustrating.
On that note, is there a community online where one can seek out mentorship. It doesn;t have to be a community of who's who - just some decent nice people with common sense and desire to succeed should suffice. I am at a stage where I could use some advice as well.